29344-64-7

Upstream product

• 29345-05-9 2,3,4,5-Tetraaethylbenzylchlorid 
• 928-49-4 hex-3-yne 
• 4873-09-0 allyl tosylate 
• 624-65-7 2-propynyl chloride 
• 642-32-0 1,2,3,4-tetraethylbenzene 

Relevant academic research and scientific papers

Reaction of zirconacyclopentadienes with electrophiles such as benzaldehyde, methyl methacrylate and 1-bromo-2-butyne after treatment with RLi

Zirconacyclopentadienes reacted with electrophiles after treatment with alkyllithium. For example, the reaction with benzaldehyde after treatment with methyllithium to give a nucleophilic addition product of a dienyl moiety to aldehyde, dienylcarbinol, in a moderate yield. Similar reaction of a zirconacyclopentadiene using butyllithium with methyl methacrylate afforded a Michael addition product in a good yield. Treatment of zirconacyclopentadienes with n-BuLi followed by 1-bromo-2-butyne gave a mono-propargylated diene derivative in 95% yield after hydrolysis. When propargyl chloride was treated with n-BuLi first and then added to zirconacyclopentadienes, penta-substituted benzene derivatives were formed in high yields.

Palladium-catalyzed benzannulation from alkynes and allylic compounds

Various alkynes reacted with allyl tosylates in the presence of palladium catalysts, giving polysubstituted benzenes with good to high regioselectivity. Pentasubstituted and trisubstituted benzenes were readily prepared by reaction of internal alkynes and

Benzannulation from alkynes and allyl tosylates via a π-allylpalladium intermediate

(Graph presented) Allyl tosylate is a good allyl source for a novel palladium-catalyzed benzannulation that affords polysubstituted benzenes from 1 mol of an allyl compound and 2 mol of internal alkynes. Using triphenyl phosphite as a ligand, the reaction with terminal alkynes gave trisubstituted benzenes regioselectively.